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#$Date: 2019-11-24 16:05:55 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238474 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/76/7237655.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7237655
loop_
_publ_author_name
'Liu, Yingle'
'Zhao, Gang'
'Tang, Yongxing'
'Zhang, Jichuan'
'Hu, Lu'
'Imler, Gregory H.'
'Parrish, Damon A.'
'Shreeve, Jean'ne M.'
_publ_section_title
;
 Multipurpose [1,2,4]triazolo[4,3-b][1,2,4,5] tetrazine-based energetic
 materials
;
_journal_issue                   13
_journal_name_full               'Journal of Materials Chemistry A'
_journal_page_first              7875
_journal_paper_doi               10.1039/C9TA01717H
_journal_volume                  7
_journal_year                    2019
_chemical_formula_moiety         'C3 H N8 O2, H4 N O'
_chemical_formula_sum            'C3 H5 N9 O3'
_chemical_formula_weight         215.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-12-12 deposited with the CCDC.	2019-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 125.781(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.224(2)
_cell_length_b                   5.5034(7)
_cell_length_c                   10.7701(13)
_cell_measurement_reflns_used    1800
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.58
_cell_measurement_theta_min      3.10
_cell_volume                     780.13(17)
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4410
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.068
_diffrn_reflns_theta_min         3.095
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_crystal_colour            'clear orange'
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.121
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2145
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0509P)²+0.2064P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0922
_reflns_Friedel_coverage         0.941
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.915
_reflns_number_gt                1894
_reflns_number_total             2145
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ta01717h2.cif
_cod_data_source_block           shrv746
_cod_original_cell_volume        780.15(17)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7237655
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.981
_shelx_estimated_absorpt_t_max   0.994
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.40676(19) 0.2572(4) 0.2588(3) 0.0443(6) Uani 1 1 d . .
O2 O 0.29696(16) 0.5479(5) 0.1876(2) 0.0471(6) Uani 1 1 d . .
N3 N 0.3802(2) 0.4559(5) 0.2833(3) 0.0315(5) Uani 1 1 d . .
N4 N 0.45021(17) 0.5545(4) 0.4197(2) 0.0269(5) Uani 1 1 d . .
C5 C 0.42303(19) 0.7611(5) 0.4566(3) 0.0220(5) Uani 1 1 d . .
N6 N 0.33488(16) 0.8802(5) 0.3980(2) 0.0273(5) Uani 1 1 d . .
N7 N 0.35220(16) 1.0794(5) 0.4859(3) 0.0277(5) Uani 1 1 d . .
C8 C 0.45047(18) 1.0791(5) 0.5983(3) 0.0222(5) Uani 1 1 d . .
N9 N 0.50412(18) 1.2392(4) 0.7151(3) 0.0287(5) Uani 1 1 d . .
N10 N 0.60004(19) 1.1958(5) 0.8127(3) 0.0323(5) Uani 1 1 d . .
C11 C 0.6431(2) 0.9948(5) 0.7931(3) 0.0309(6) Uani 1 1 d . .
H11 H 0.7124 0.9725 0.8662 0.037 Uiso 1 1 calc R U
N12 N 0.59738(16) 0.8337(4) 0.6837(2) 0.0265(5) Uani 1 1 d . .
N13 N 0.49682(14) 0.8842(4) 0.5838(2) 0.0200(4) Uani 1 1 d . .
O14 O 0.62488(19) 0.3150(5) 0.5336(3) 0.0521(7) Uani 1 1 d D .
H14 H 0.580(3) 0.421(7) 0.504(6) 0.078 Uiso 1 1 d D U
N15 N 0.70244(17) 0.4794(4) 0.5796(3) 0.0283(5) Uani 1 1 d . .
H15A H 0.6858 0.5735 0.5009 0.042 Uiso 1 1 calc R U
H15B H 0.7594 0.3991 0.6125 0.042 Uiso 1 1 calc R U
H15C H 0.7119 0.5710 0.6551 0.042 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 N3 O1 121.6(3)
O2 N3 N4 124.3(2)
O1 N3 N4 114.1(3)
N3 N4 C5 116.6(2)
N6 C5 N4 134.9(2)
N6 C5 N13 107.3(2)
N4 C5 N13 117.8(2)
C5 N6 N7 109.5(2)
C8 N7 N6 106.4(2)
N7 C8 N9 128.7(2)
N7 C8 N13 110.2(2)
N9 C8 N13 121.2(2)
N10 N9 C8 116.7(2)
N9 N10 C11 119.8(2)
N12 C11 N10 127.4(3)
N12 C11 H11 116.3
N10 C11 H11 116.3
C11 N12 N13 111.2(2)
N12 N13 C5 129.6(2)
N12 N13 C8 123.7(2)
C5 N13 C8 106.62(19)
N15 O14 H14 95(4)
O14 N15 H15A 109.5
O14 N15 H15B 109.5
H15A N15 H15B 109.5
O14 N15 H15C 109.5
H15A N15 H15C 109.5
H15B N15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N3 1.258(3)
O2 N3 1.231(4)
N3 N4 1.338(3)
N4 C5 1.360(3)
C5 N6 1.348(4)
C5 N13 1.360(3)
N6 N7 1.367(3)
N7 C8 1.323(3)
C8 N9 1.355(3)
C8 N13 1.370(3)
N9 N10 1.293(3)
N10 C11 1.389(4)
C11 N12 1.305(4)
C11 H11 0.9300
N12 N13 1.358(3)
O14 N15 1.385(4)
O14 H14 0.841(14)
N15 H15A 0.8900
N15 H15B 0.8900
N15 H15C 0.8900
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11 N6 0.93 2.65 3.333(4) 130.5 4_565
O14 H14 N3 0.841(14) 2.68(4) 3.333(4) 136(5) .
O14 H14 N4 0.841(14) 1.88(2) 2.685(3) 159(5) .
N15 H15A N10 0.89 2.09 2.939(3) 159.6 2_574
N15 H15B O1 0.89 2.13 2.988(3) 161.9 4
N15 H15B O2 0.89 2.55 3.168(3) 127.2 4
N15 H15B N3 0.89 2.61 3.387(3) 145.9 4
N15 H15C O2 0.89 2.42 2.896(4) 113.8 4_565
N15 H15C N6 0.89 2.19 2.890(3) 135.3 4_565
N15 H15C N12 0.89 2.51 3.194(3) 133.9 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O2 N3 N4 C5 4.8(4)
O1 N3 N4 C5 -175.8(2)
N3 N4 C5 N6 11.8(4)
N3 N4 C5 N13 -170.7(2)
N4 C5 N6 N7 178.2(3)
N13 C5 N6 N7 0.6(3)
C5 N6 N7 C8 -0.6(3)
N6 N7 C8 N9 -179.7(3)
N6 N7 C8 N13 0.3(3)
N7 C8 N9 N10 178.8(3)
N13 C8 N9 N10 -1.3(4)
C8 N9 N10 C11 0.9(4)
N9 N10 C11 N12 -0.4(5)
N10 C11 N12 N13 0.1(4)
C11 N12 N13 C5 -179.1(3)
C11 N12 N13 C8 -0.5(3)
N6 C5 N13 N12 178.5(2)
N4 C5 N13 N12 0.4(4)
N6 C5 N13 C8 -0.4(3)
N4 C5 N13 C8 -178.5(2)
N7 C8 N13 N12 -178.9(2)
N9 C8 N13 N12 1.1(4)
N7 C8 N13 C5 0.0(3)
N9 C8 N13 C5 -180.0(2)
